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Abietane and Nor-Abitane Diterpenoids from the Roots of Salvia

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Abietane and Nor-Abitane Diterpenoids from the Roots of Salvia Eghtesadi et al. SpringerPlus (2016) 5:1068 DOI 10.1186/s40064-016-2652-0 RESEARCH Open Access Abietane and nor‑abitane diterpenoids from the roots of Salvia rhytidea Farrokh Eghtesadi1, Mahdi Moridi Farimani2*, Nourallah Hazeri1* and Jafar Valizadeh3 Abstract Background: The genus Salvia is a rich source of structurally diverse terpenoids. Different species of the Salvia have been used in folk medicine of Iran and therefore attracted the attention of researchers for exploring their chemical constituents. In a project directed at structurally interesting bioactive metabolites from Iranian Lamiaceae, we studied Salvia rhytidea. Results: Fractionation of the petroleum ether extract of the root of S. rhytidea led to the isolation of a new 20-nor- abietane diterpenoid (1), together with seven known compounds, comprising five abietane diterpenoids (2–6), and two rearranged abietanes (7, 8). Their structures were established by a combination of 1D and 2D NMR. Conclusions: Our results showed that the root of S. rhytidea could be considered as a new and rich source of differ- ent types of abietane and rearranged abietane diterpenoids. Keywords: Salvia rhytidea, Diterpenoid, Abietane, Solvent extraction, Column chromatography, Structure elucidation Background et al. 2015; Moridi Farimani et al. 2008), we investigated The genus Salvia is a rich source of structurally diverse the petroleum ether extract of the root of S. rhytidea. terpenoids (Kintzios 2000; Moridi Farimani et al. 2013). Here we report the isolation and structure elucidation of Among these, numerous diterpenoids with promising 1-deoxo aurocadiol (1), as a new 20-nor-abietane diter- bioactivities, such as antileishmanial, antitumor, antimi- penoid. In addition, the abietane diterpenoids ferruginol crobial, antifungal properties, have been reported from (2), taxodione (3), arucadiol (4), deoxyneocryptotanshi- Salvia species (Ebrahimi et al. 2013; Tan et al. 2002; none (5), and 7α- Ethoxyroyleanone (6), and rearranged Akaberi et al. 2015; Moridi Farimani and Miran 2014; abietanes microstegiol (7) and 12-hydroxysapriparaqui- Ulubelen 2003; Jassbi et al. 2006). The most abundant none (8) were isolated and are described here for S. rhyt- diterpenoids in the genus are abietanes and rearranged idea for the first time. abietanes (Wu et al. 2012). The genusSalvia is repre- sented in the Iranian flora by 61 species, of which 17 are Results and discussion endemic (Jamzad et al. 2012). Salvia rhytidea Benth is an Compound 1 (Fig. 1) was isolated as an orange, amor- endemic species that grows widely in the eastern parts of phous solid. The IR spectrum showed absorptions of Iran (Rechinger 1987). In our efforts to discover new and hydroxy (3475 cm−1) and olefinic (1610 cm−1) function- potentially bioactive secondary metabolites from Iranian alities. The13 C NMR spectrum showed 19 carbon reso- Salvia species (Moridi Farimani and Mazarei 2014; Ebra- nances, which were identified with the aid of HSQC and himi et al. 2014; Moridi Farimani et al. 2012; Bahadori DEPTQ spectra as four methyl, three methylene, four methine, and eight quaternary carbons. The 13C NMR spectrum showed signals indicative of ten aromatic car- 1 *Correspondence: [email protected]; [email protected] bons. The H NMR spectrum showed resonances of two 1 Department of Chemistry, Faculty of Science, University of Sistan methyl singlets at δH 1.22 (s, 6H). Resonances of two and Baluchestan, Zahedan, P.O. box 98135‑674, Iran 2 Department of Phytochemistry, Medicinal Plants and Drugs Research additional methyl groups at δH 1.14 (d, J = 6.9 Hz) and Institute, Shahid Beheshti University, G. C., Evin, Tehran, Iran 1.19 (d, J = 6.9 Hz), together with a signal at δH 2.90 Full list of author information is available at the end of the article © 2016 The Author(s). This article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. Eghtesadi et al. SpringerPlus (2016) 5:1068 Page 2 of 6 16 OH OH O 12 15 HO HO 11 13 17 1 10 14 2 9 8 3 7 4 5 6 19 18 O 1 2 3 OH OH OH HO O O O O O O 4 5 6 OH O O OH 7 O 8 Fig. 1 Structure of compounds 1–8 (sept, J = 6.9 Hz) indicated the presence of an isopro- were observed at δC 18.5, 148.8, and 126.5, respectively, pyl moiety. Signals at δH 7.02 (d, J = 7.0 Hz) and 7.43 with upfield shifts of ca. 18, 10, and 11 ppm relative to (d, J = 7.0 Hz) were indicative of two aromatic protons arucadiol, while the chemical shift of C-3, C-6, C-9, and with ortho-position to each other. Another aromatic C-10 were observed at δC 38.0, 129.8, 128.4, and 134.6 methine signal appeared as a singlet at δH 6.78. There- with downfield shift of ca. 3, 10, 9, and 10 ppm, respec- fore, the structural features were reminiscent of a nor- tively. These observations suggested the replacement of abietane diterpenoid containing two aromatic rings. The the C-1 carbonyl with a methylene group. HMBC cor- NMR data of 1 showed great similarity to those of aru- relations (Fig. 2) between H-1 (δH 2.78, 2H, t), and C-2 cadiol isolated from S. argentea (Michavila et al. 1986) (δC 18.5), C-5 (δC 148.8), C-10 (δC 134.6), and C-9 (δC and S. miltiorrhiza (Ginda et al. 1988). Inspection of the 128.4), and COSY correlation between H-1 and H-2 (δH 13C NMR spectra showed the lack of a carbonyl group in 1.72, 2H, m) confirmed the location of the methylene compound 1 but the presence of an additional methylene group. Unambiguous assignments of NMR data were group at δC 27.6. The chemical shifts of C-2, C-5, and C-7 achieved by a combination of COSY, HMQC, and HMBC Eghtesadi et al. SpringerPlus (2016) 5:1068 Page 3 of 6 Deoxyneocryptotanshinone ( ) is a para-quinone abit- OH 5 anne diterpenod with cytotoxic activity which was iso- lated from S. miltiorrhiza for the first time (Ikeshiro et al. HO 1991). 7α-Ethoxyroyleanone (6) has been reported from S. lavandulaefolia, S. lanigra, and Peltodon longipes and its cytotoxic and antioxidant effects were investigated (Fronza et al. 2011; Shaheen et al. 2011; Michavila et al. 1985; Burmistrova et al. 2013). Microstegiol (7) is a rearranged abietane with a seven- member ring skeleton. This compound has solely been reported from Salvia genus so far (Topcu et al. 2013; Ulubelen et al. 1992). It has been shown to have mild antibacterial effects (Topçu and Gören 2007). 12-hydroxysapriparaquinone (8), a rearranged Fig. 2 Key HMBC correlations of 1 4,5-seco-abietane diterpenoid, previously isolated from S. limbata (Topcu et al. 1996). Experimental experiments. Compound 1 was therefore established General experimental procedures structurally as 1-deoxo-arucadiol. NMR spectra were recorded at a target temperature Ferruginol (2) is a well known abietane diterpenoid of 18 °C on a Bruker Avance III 500 MHz spectrometer which was isolated from different Salvia species such operating at 500.13 MHz for 1H and 125.77 MHz for 13C. as S. syriaca and S. sclarea (Ulubelen et al. 2000, 1994). 2D NMR experiments (1H-1H COSY, HSQC, HMBC, Antileishmanial (Tan et al. 2002), antimicrobial (Ulubelen NOESY) were performed using Bruker microprograms. et al. 1999), cytotoxic (Moujir et al. 1996; Fronza et al. CDCl3 was purchased from Armar Chemicals. TLC 2011), antihypertensive (Ulubelen et al. 1994), and was performed on silica gel (Merck, Kieselgel 60, F254, anticholinesterase (Topcu et al. 2013) activities were 0.25 mm) phase. Column chromatography (CC) was car- reported for ferruginol and the mechanism of its antioxi- ried out using silica gel (70–230 mesh, Merck). Flash col- dant properties was also investigated (Saijo et al. 2015). umn chromatography (FCC) was performed on silica gel Taxodione (3) is a diterpenoid with quinone methide (230–400 mesh, Merck). skeleton which was reported from different genus like Taxudium, Clerodendrum, and Salvia (Machumi et al. Plant material 2010; Kolak et al. 2009; Kusumoto et al. 2009). Different The roots of Salvia rhytidea were collected from Taftan biological properties have been reported for this com- Mountain, 28°36′ N and 61°4′ E, in the Baluchistan of pound, including antibacterial (Yang et al. 2001), anti- Iran at an altitude of 2497 m, in autumn 2012. The plant oxidant (Kolak et al. 2009), antitermitic (Kusumoto et al. was authenticated by Dr. Valizadeh and a voucher speci- 2009), antifeedant (Acosta et al. 2008), antifungal (Topçu men (no. 4938) was deposited in the Herbarium of the and Gören 2007), and anticholinesterase activities (Topcu School of Biology (Dr. Akhani Herbarium), University of et al. 2013). Moreover, cytotoxic and tumor inhibitory Tehran. properties of taxodione have been investigated in in situ and in vivo experiments (Kupchan et al. 1969; Ulubelen Extraction and purification et al. 1999; Abou Dahab et al. 2007). The mechanism of The air-dried roots of S. rhytidea (2100 g) were crushed action of taxodione for its cytotoxic properties was inves- and extracted with petroleum ether (bp. 40–60 °C) at tigated in several articles with focus on its DNA binding room temperature (25 °C) for 5 days. The extract was con- and DNA damaging character (Zaghloul et al. 2008), and centrated in vacuo, to afford 12.6 g dark gummy residue.
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